Comment by AshamedCaptain

Wouldn't you target whatever is the minimum "supported" glibc you want to run in the first place? What is that you need to recompile?

Chroot _is_ trivial. I actually use it for convenience, as I could also as well install the older toolchains directly on the newer system, but chroot is just plain easier. Maybe VS has a button where you can target whatever version MS fancies today ("for a limited time offer"), but what about _any other_ windows toolchain?